Gay Crossdressing Stories

GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.

Walking the dog leads to more (ch. 2)

By Frankfurt Chronicler 12 Dec 2022

We almost get away with it, but Lars' friends find us and want a piece of the action. This is another long read, but with a ton of sex.

9.3 (20) 2541 22 Min Comments

My first dressing up (ch. 2)

By Jennfair 9 Dec 2022

Continued my first experience as a sissy and my mom grooming me. First experience with my first cock

8.9 (27) 3979 8 Min Comments

Instructor Mike's Academy

By qtaimee 9 Dec 2022

A sheltered an innocent south asian teen with a mostly absent finder finds his Superior White Daddy on the fledgling internet in the early 90s. Can Instructor Mike mold the little peepee girl into his perfect sissy to service his Tremendous White Cock? Class is in session for little aimee. (Parts 1-6)

8.7 (13) 5804 140 Min Comments

Heather (ch. 6)

By Heather_xd 7 Dec 2022

Been a delay but here is the continuation of the whore Heather

4.0 (5) 605 1 Min Comments

Bodybuilder's Bitch

By Victor 26 Nov 2022

College athlete wears lingerie for two bodybuilders from his gym.

9.4 (99) 14053 10 Min Comments

A man see me in panties became an obsession (ch. 3)

By rivi 17 Nov 2022

Meeting strangers for sex is a world in itself . Most men attending outdoor cruising areas are not crossdressers but have a range of sex desires which have to be approached appropriately

8.0 (9) 4095 4 Min Comments

Michelle

By Oldfinger 10 Nov 2022

Stepping out to a dance hall I encounter a totally new shemale experience. Lovely girl.

8.8 (12) 1017 12 Min Comments

Sissy training (ch. 4)

By Viki 2 Nov 2022

This is a story of how I found a mistress and transformed into my true self. The story is from my point of view, and it all takes place in 14 days. This story is slow with lots of details, and not only sex. There is a little something for everyone, so if you This is a story of how I found a mistress don't like something feels free to skip the day, but you might miss something. Hope you enjoy it.

9.4 (12) 2545 21 Min Comments

My first time with a man

By Jennfair 6 Oct 2022

How I turned a sexy chat into super hot sex with a man for the first time.

9.1 (22) 4734 11 Min Comments

Discovery of a new Sissy

By Payalji 24 Sep 2022

My sissy journey from a boy to a sissy whore.

7.2 (23) 6760 4 Min Comments

I became a sex slave

By Viki 16 Sep 2022

This is a story of how my normal life changed and i became an obedient sissy for, my master.

8.4 (39) 10774 21 Min Comments

The CC Society

By bootlicker 6 Sep 2022

The merging of two of my stories published on another site. Two feminized sissies are sold to dominant sadists who plan to use and abuse them for their pleasure.

8.9 (19) 5010 38 Min Comments

Unforgettable summer (ch. 3)

By Viki 29 Aug 2022

Part 3 follow-up on "A normal relationship turned into a wild weekend orgy". The names and places of this story are not real.

8.7 (7) 977 16 Min Comments

A normal relationship turned into a wild weekend orgy (ch. 2)

By Viki 25 Aug 2022

Continuation of the story "A Normal Relationship Turned Into A Wild Weekend Orgy" This is the events of the said weekend,

8.6 (22) 2260 15 Min Comments

A unexpected turn of events

By Viki 20 Aug 2022

An unexpected surprise, that led to an interesting experience

7.6 (33) 4897 6 Min Comments

Getting fucked by grinder date in hotel (ch. 2)

By zeenatcd 20 Aug 2022

After we met first time at hotel we started talking about fantasy of each other and started fulfill them. So this was his first fantasy.

7.6 (7) 5340 7 Min Comments

Taken for the first time, but not the last

By Disbtm 9 Aug 2022

A young traveler's car breaks down and he finds himself tied down to a kitchentable, crying and loosing his anal virginity.

9.2 (79) 12512 11 Min Comments

PrincessBoy Diaries

By BeefyFem 8 Aug 2022

Daddy has fun surprises in store for his boy princess as they mix business and pleasure in Palm Springs

9.3 (38) 5795 13 Min Comments

What I Want

By Victor 1 Aug 2022

Tall, massively muscular Brodin is a no nonsense bottom with many fuck buddies. One night a married fuck buddy asks him to slip on a pair of panties. To Brodin's surprise, he likes it and so starts a new kink for the big, broad bodybuilder.

9.4 (71) 5134 20 Min Comments

Lifechanger

By Cirkle7 26 Jul 2022

I get fucked and like it!

8.5 (35) 5877 9 Min Comments

Bottom boy at antique store (ch. 3)

By cut 9 Jul 2022

Like a bitch

8.8 (26) 4115 2 Min Comments

Sissie

By Mikal 9 Jul 2022

My name is Sissie it used to be Matt, but that name doesn’t fit. I just put up a sissy pride flag in my window. Mine has pink and white stripes with a modified phallus symbol that looks like a heart with a limp arrow jutting out of it.

8.4 (15) 2679 5 Min Comments

The Rest Stop Digest - The Jill Jordan story (ch. 2)

By SkylarWinterLouis 2 Jul 2022

Although this is ch 4 , it is the 2nd part of the Jill Jordan story.

8.1 (12) 1487 12 Min Comments

A journey of transformation

By Vikktor 14 Jun 2022

I finally found someone that could help me fulfill my desires.

8.9 (49) 10233 17 Min Comments

Cross dressing Cumslut

By SoooperFreakk 10 Jun 2022

CD Cumpdump and fun freak meet up

8.4 (15) 4401 2 Min Comments

Summer of My Life

By Roxxi 1 Jun 2022

I Was thinking about Tony' s cock, and as I slid a black lace g string up to my hips and tucked my clit back.

5.6 (7) 1447 2 Min Comments

Becoming Ms. Dee Praved

By Ms. Dee Praved 26 May 2022

I venture out to explore my sexuality, and meet a more experienced crossdresser and her friend. He takes us both and uses us well. This is a true story.

8.9 (27) 2411 7 Min Comments

CEO

By Victor 24 May 2022

My hot DILF CEO is an alpha with a soft side when we're alone. The older muscle stud wants nothing more than my younger, muscular body to dominate him and make him my bitch.

9.2 (75) 10299 35 Min Comments

Crossdresser Confessions

By Ms. Dee Praved 23 May 2022

The true story of one of my favorite guys from Craigslist. He was a horny young soldier just looking to come. Of course I eagerly offer my mouth and ass to him.

8.7 (16) 2602 5 Min Comments

Let's Play Dress Up

By James Stone 21 May 2022

"If it's not a big deal, then you do it," I said. He shrugged and got up, going to the box. He dug around until he came up with another bra, a little nicer than the one I was holding, pink lace and pink satin. He held it up and then slipped his arms through the straps, holding it against his chest, over his shirt. He tried to reach around back to close it, but couldn't...

9.3 (41) 4666 14 Min Comments